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Paper | Special issue | Vol 64, No. 1, 2004, pp.153-175
Published online, 18th May, 2004
DOI: 10.3987/COM-04-S(P)8
Chemistry of Indoles Carrying a Basic Function. Part IX. Unexpected Cyclizations of Diketones Derived from Uhle’s Ketone

István Moldvai,* Eszter Gács-Baitz, Eszter Temesvári-Major, Mária Incze, László Poppe, and Csaba Szántay*

*Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H-1025 Budpest II, Pusztaszeri ut 59-67, P.O. Box 17, Hungary

Abstract

Starting from a tricyclic diketone (14) obtained by Bowman’s method, a tetracyclic oxonaphthalene derivative (17) has been prepared through intramolecular aldol condensation followed by indole → naphthalene isomerization. An unexpected formation of a lactol ether (16) was observed as a result of acidic treatment of 14. Two modified reaction sequences starting from N-methyl derivatives have also been presented. The keto ketal (26) gave a macrocyclic lactol (27) with unexpected structure as a result of deketalization with trimethylsilyl iodide. The formation of a tetracyclic lactam (37) was observed while applying the modified Reformatsky reaction to ketone (33).